


Jealous

by chilly83



Category: Chicago PD (TV)
Genre: Upstead
Language: English
Status: Completed
Published: 2020-05-08
Updated: 2020-05-08
Packaged: 2021-03-02 18:07:19
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 9,707
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24031042
Author URL: https://archiveofourown.org/users/chilly83/pseuds/chilly83
Summary: Hailey comes back to Chicago, with her FBI partner.
Relationships: Hailey Upton & OA Zidan, Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Comments: 23
Kudos: 96





	1. Chapter 1

**Author's Note:**

> Thank you readers for all your support on the other fics I wrote! This is a short fic about Jay and OA meeting, inspired by some musing on tumblr about jealous Jay. I really wanted to write a jealous Jay fic, so here it is! I hope Jay isn’t too out of character. I tried to stay true to how he has acted when he was upset in previous episodes, but it might be slightly OOC. 

For the first time in 5 weeks, Hailey and Jay woke up with smiles on their faces. Since Hailey left for New York, the alarms they set to wake up only seemed to serve one purpose: bringing them back to the reality of another day separated. Today, however, their alarms served a new purpose, a much more exciting reality. Because when they woke up today, they knew, they would get to see each other again. 

Jay busied himself with monotonous chores. He had asked for the day off from Voight. He wanted to pick up Hailey from the airport and knew that there was no way that he would be able to sit at his desk for the morning and concentrate on work. He figured if he spent the morning cleaning his apartment, running some errands and working out, that would help him get to 11:47 faster. He just needed to make it a few more hours and then he would finally be reunited with Hailey. And as a bonus, he would get to meet her partner from the FBI.

Hailey had told Jay a lot about OA. He was excited to hear that she was working with an Army Ranger. He knew that this meant her life was in good hands. She also had a lot of fun working with him and had told Jay that OA reminded her of him, except for when it came to his taste in pizza. So, when she said that OA was coming to Chicago with her to meet with the Gangs unit over at the 47th, he offered to pick them both up. He preferred to have Hailey all to himself, but he figured that he could at least extend the professional courtesy to OA. He was relieved however, when OA declined the offer. Apparently, the sergeant over Gangs wanted to make a good impression with the FBI so he would be picking him up personally from the airport. Now all he had to do was stay busy until it was time.

Hailey was ready to go as soon as her alarm went off. She had packed her suitcase the night before and had her clothes set out for the next day. She had to run into the office one last time to say goodbye to the New York team but then she was off to the airport. When the SAC found out Hailey’s flight info, she booked a seat for OA to go along. The Latin Kings gang had recently sprung up in New York and the FBI was desperate to get intel on it. Since it originated in Chicago, she thought that sending an agent over to the Gangs Unit to get as much information as they could about the gang would really help them out. With Hailey having worked for both the Chicago PD and FBI, she figured that the perfect time to do it would be when Hailey went back, that way she could act as a liaison of sorts between the two. 

Hailey was excited to hear about the arrangement. She really enjoyed working with OA and could not wait to show him around Chicago and her team. She had extended Jay’s offer to pick up OA to him but was disappointed when he had to decline when the gang unit’s sarge insisted on picking him up. Before they knew it, it was time to say goodbye the New York field office and head to the airport. OA knew how excited Hailey was to get back to her partner, but he resisted the urge to tease her. He had come to realize that she was in love with her partner, but there was something about the way that she talked about them gave him the impression that she had not acted on her feelings. As they handed their boarding passes to the flight attendant, OA placed a reassuring hand on her shoulder.

“Almost home partner.”

Hailey smiled at OA and tried to control her nerves. Just a few more hours and she would be with Jay again.

When Jay checked the airport’s arrivals, he found that Hailey’s plane had landed early. His heart rate quickened and he rushed to the listed gate hoping to get there before she got off the escalator. He was not sure what he was going to do when he saw her. He was arguing with the voice in his head that kept yelling at him to sweep her off her feet and kiss her, settling instead for a welcome home hug, when he saw them. 

There was a time in his life when Jay was referred to as a lady’s man. It had been his experience in bars, nightclubs, even just grocery stores, all it took to get a lady’s number was for him to flash a smile and a little charm. He was never lacking in the confidence department and never really felt the pang of jealously when it came to competition. So, when he saw the man standing with Hailey, the one that had his arm around her shoulder, the one that was leaning down and saying something into her ear, he was not sure how to feel. 

The man was tall, taller than him, wearing a really nice suit, nicer than anything Jay had ever owned. He suddenly started to feel warm when he saw Hailey throw her head back and laugh out loud at whatever was said to her. Until that moment he was sure that he was the only one that could make her do that. To see this other man, her partner from New York he could only assume, illicit that same response from her, all those fun times Hailey talked about in New York took on a new meaning. Jay began to imagine them eating dinner in a dimly lit restaurant, their hands slightly brushing against each other as they walked back to OA’s car, the way he leaned down for a kiss as he opened the door for Hailey. Jay suddenly found himself very unsure of how Hailey felt about him. He thought all their talks were happening because she missed him but now, he had this nagging feeling that she was simply telling her best friend about this new man in her life. 

Before he realized how lost in his thought he was, he heard Hailey calling his name. 

“Jay!” Hailey yelled as she excitedly bounced her way to Jay. She reached her arms out as if to give Jay a hug but froze when he just stood there. Hailey found herself dropping her arms to her sides and tried to quickly recover before anyone noticed.

“Hey partner!” She said excitedly trying to hide her embarrassment. 

“Hey! Saw you landed early.” Jay said as he nodded a hello to them. 

“Umm. This is OA. OA, this is my partner Jay!” Hailey said as she introduced the two men.

OA and Jay extended hands out to each other and shook. 

“First time in Chicago?” Jay cringed at his lame attempt at small talk.

“Ya. Luckily I have heard good things. I’m excited to spend the week here.” OA said as Jay turned and began walking to the baggage claim. Hailey and OA followed behind him.

“So, latin players are moving in New York I hear.”

“Ya. We have run into them a couple of times. Bosses figured the best place to get information would be straight from the Chicago PD.” OA stood by the carousel as he spoke. Jay was looking for the bag that Hailey had when he dropped her off at the airport but before he had a chance to grab it, OA had it in his hands. He pulled it off the carousel with ease, popped the handle out and handed it to Hailey. The smile on Hailey’s face would normally make Jay’s heart skip a beat but today, seeing it directed at another man, it made his heart drop.

“They didn’t want to just tell you the info over the phone?” Jay hoped that they didn’t notice the bite in his tone. When he saw Hailey staring at him, eyes narrowed like she was trying to figure him out, he knew that they noticed.

“No” OA chuckled, “they thought it would be best if I drove around, got to see how these guys operate.” Jay nodded, relieved that OA didn’t react to the tone.

When they got near the exit of the airport, OA noticed a man holding a sign with his name.

“That must be my ride. Jay,” OA said while reaching a hand out again, “it was great to finally meet you.”

“Likewise” Jay said as he returned the handshake “I am sure I’ll see you around again.” He said with a kind smile.

“Alright Chicago.” OA said as he pulled Hailey in for a side hug “I’ll see you tonight partner.”

“Don’t eat anything! Seriously! You’ll ruin your appetite for dinner!” Hailey responded. 

She was so excited about being back home with Jay that she did not even notice that he seemed to be a bit distant. When she turned back around to Jay he had already started walking off towards his truck. This was not the reunion he had imagined in his head and suddenly it was really hard to be around Hailey.


	2. Chapter 2

**Notes for the Chapter:**

> Thank you for giving the story a chance! I appreciate all the kudos and comments! Looks like this is going to be longer than I thought. I am hoping I can wrap it up with 4 chapters!

Hailey would be lying if she said she wasn’t disappointed that she didn’t get a welcome home hug from Jay. Actually, now that she is thinking about it, nothing about her return was going how she planned. She thought that Jay would be more excited to see her. She hadn’t been able to stop smiling since she woke up knowing that she would be with him again. Hailey began to worry that something was wrong. She had kept in touch with him and Vanessa while she was gone. Neither one of them mentioned any tough cases or that Jay was struggling with demons again. She sadly began to wonder if maybe he didn’t feel the same way about her. Maybe all those stolen glances she caught him with were in her head. Maybe telling him how she felt wasn’t such a good idea. The car ride was uncomfortably silent, and she wasn’t used to uncomfortable silences when it came to Jay.

“I missed you.” Hailey said, testing the waters.

“Me too.” Jay said as he sadly smiled at Hailey.

“What are your plans for the day? I thought after I talked to Hank you could duck out for a couple of hours. Maybe we can catch up, grab lunch?” Hailey asked hopefully.

Jay pondered her question. He was so happy to see her; he wanted to spend his whole day with her. At the same time, he was not expecting to see her so friendly with her New York partner. Jay and Hailey had been partners for years, they have almost died in front of each other, they’ve dodged bullets, fought criminals and had many drunken nights together but they had never hugged. If she is already hugging this new guy, it must be because there is more going on there. 

“I actually got a lot of work I need to get done.” He said. Hailey picked up on the disappointment in his voice.

“Maybe I can help you. I was really wanting us to spend time together. I thought we could take OA out and show him some of the Chicago highlights.”

“He’s here for a week, right? I am sure we will get some time.” Jay smiled at her when he said that but deep down, he was hoping that he wouldn’t have to see her FBI partner again.

“I made reservations tonight. Giardano’s for the 3 of us!”

“Ya? Let me check with Will. He was having some issues he needed help with. I’ll let you know if I’m available.” Hailey could tell that something was bothering Jay and she didn’t want to push it, so she accepted his answer. 

***********

When they arrived at the district, Hailey was relieved that the rest of the unit greeted her with a round of hugs and welcome homes. She was nervous when Hank approached her. The last time they saw each other, it did not go well. Jay noticed her tense up when he walked over to her. On instinct, he moved next to her and put his hand on her lower back, hoping that would let her know he was right there with her. He had heard from Vanessa about the last meeting between Hank and Hailey. She told him about it over beers at Molly’s one night. Upon hearing the story, Jay went straight to Hank’s house and banged on the door until he answered. The shouting match that ensued was one that Jay didn’t think he could recover from. He thought for sure that the following day he would be told to pack up his shit, but luckily it seemed like Hank had calmed down since the previous night. He called Jay into his office and apologized for the way he treated Hailey. Both in a much better head space, they were able to have another conversation about what had happened, letting each of them to express their concerns for Hailey’s well-being. The talk was ended with a hug, but Jay never told Hailey about any of it. He knew that she was probably unsure of where she stood with Hank.

“Welcome home kid.” Hank said as he gave Hailey a soft shoulder squeeze. 

“Join me in my office please.” Hank said as he walked away. Hailey found herself frozen where she stood; that night flooding back to her. She looked back at Jay, not sure what to expect. 

“I can go with you, but I think you need to go alone.” He said as he gave her a reassuring smile. 

Hailey nodded hesitantly, still unsure of what Hank would be saying about her time spent in New York. Sensing her hesitation, Jay grabbed one of her hands, giving it a light squeeze while looking her in the eyes and nodding. He wanted to tell her that she had nothing to be afraid of, that she could handle anything, that she was the strongest and bravest woman he had ever met. And when he saw the flash of confidence find its place in her eyes again, he knew that she had heard him. She nodded at him with a smile and walked into Hank’s office.

Hailey was relieved when Hank began to commend her on her work with the FBI. She knew he had been checking up on her, but she had avoided any contact with him while she was gone. 

“I’m really proud of the work you did. On a professional and personal level.” Hank knew about her talks with Jay. He had asked Jay how she was doing, knowing they talked every day. Jay had assured him that she understood what happened and was working through it. Without giving away details of their private conversations, he let Hank know that Hailey was seeing things more clearly now, the lines no longer blurred. 

“Thanks, sarge.” Hailey said with a smile.

“I understand you are going to be over at the 47th with your partner this week. I hope this is just temporary and you’ll be back with the unit next week.” Hank stated hopefully.

Hailey was hoping she would be able to rejoin Intelligence but after weeks of avoiding Hank, she wasn’t sure where she stood.

“Ya. I’ll be back.” She said trying to keep her emotions at bay. She felt her eyes begin to fill up with water so she instinctively looked away, not wanting Hank to see her cry. 

“Hailey.” Hank said as she stood up to walk to the other side of his desk. HE sat on the edge and faced her. “What you did……” Hank looked down at the ground “how I reacted….”. Hank struggled to find his words. “I’ve lost Al. I’ve lost Erin. Antonio. I could not lose another person. I was scared. I let fear get control of me. I’m sorry for what happened.” 

Hank looked at Hailey as her eyes met his. Hailey was shocked. She had not expected an apology, and she certainly hadn’t expected to hear Hank express fear of losing her. At a loss for words, she simply nodded in understanding.

“I’ll see you next week then.” Hank said as he walked back to his seat. “Tell Halstead to see me before you guys leave.”

“Sir?” Hailey was confused at his comment. Why did Hank think they were leaving together?

“I figured he took the day off to spend with you. Send him in before you leave.” Hailey tried to process Hank’s words. Jay had told her he had planned to spend the day working at catching up on things he had fallen behind on. Now she was being told by their boss that he had taken the day off to spend with her. 

“Ya. I’ll let him know.” Hailey said as she left the office. She shut the door behind her and looked over to Jay’s desk. She saw him typing away at his desk, looking lost in whatever he was doing.

“Umm, Voight wants to see you before you leave.” She said trying to gauge his reaction. The way Jay’s eyes shot open in surprise told her everything she needed to know. She was not supposed to know he was off. Hailey tried to hide the hurt in her eyes, but Jay saw right through it.

“I’m gonna head out. We can rain check on dinner if you are busy.” Hailey said sadly before Jay could say anything. 

“Ya. Sounds good.” Jay said matching Hailey’s disappointment. He knew the right thing to do was to stop her, explain what was happening. But that would require admitting he was jealous, which would mean admitting his feelings for her and being rejected. That just wasn’t something that he could take at the moment. So instead, he watched as she said goodbye to her team, making plans to get together for drinks with OA sometime. He shot off a quick text to Will letting him know that he was available for drinks after all, and made plans to meet at Molly’s that night.

********

Later that night, Will found Jay sitting at the bar at Molly’s already a few beers into his night.

“What happened?” He said as he pulled up a seat next to Jay.

“I don’t know. What happened?” Jay shot back. “They aren’t all mine.” He said, noticing that Will was looking at the collection of beer bottles next to him.

“Why aren’t you with Hailey?” Will asked. Jay had been talking about her return for weeks now. The last thing he expected to get that day was a text from Jay saying yes to drinks. 

“She had a better offer.” Jay responded. Just then an attractive woman appeared at Jay’s side. Jay shot her a small grin as she sat next to him and grabbed one of the beer bottles. Will’s eyes widened as he watched the lady lean in, placing a hand on Jay’s chest as she whispered something to him. This was the first time since Erin left a few years ago that Will had seen Jay with a woman.

“Hey there! I’m Will. Jay’s brother.” 

“Hi! Nice to meet you.” She replied. Will looked to Jay, waiting for him to join in on the conversation.

“This is, uh, a new friend I met tonight.” Jay could not remember the name of the woman who had been keeping him company for the past hour. “She is yoga instructor.” Jay was proud of himself for remembering that much.

“Candie.” She said. Will couldn’t help but chuckle. 

Will had noticed the rest of the intelligence unit sitting at a table near the front door. He was anxious to find out what was going on. He had so many questions. What’s wrong? Where is Hailey? Why is Jay over here? What is going on? 

As he tried to find a way to ask Jay without making the conversation uncomfortable, they did have an audience after all, he watched as Jay’s face turned red. Will turned to the door to see what had caused it. Now he had more questions. Who is that guy? Why is his hand around Hailey’s shoulder? Why is everyone happy to see him? Why is he touching Hailey? And just for good measure,

WHAT IS GOING ON?

**Notes for the Chapter:**

> Don't be mad at Jay and Hailey! They are two dum-dums in love and are too scared of being rejected to say anything. I can not wait to post Chapter 3!!!


	3. Chapter 3

**Notes for the Chapter:**

> This keeps getting longer! Looking to be 5 chapters now. I hope that’s ok. Thank you for reading and all the support, I love reading the comments! As soon as I wrote this Chapter I was dying to post it! I tried to wait until tonight, but I couldn’t wait. 

Will looked to Jay with a confused look on his face. At this point, Jay had begun to take long gulps of his beer and had turned his back to the group.

“Who’s the new guy?” Will asked.

“A better offer.” Jay said snidely as Hailey approached the bar. Will looked back to the group to see OA shaking hands with the group and exchanging pleasantries.

“Will!” Hailey said excitedly.

“Hailey! Welcome back!” Will said, reaching down for a hug. At least one of the Halsteads is happy to see her, she thought to herself.

“Thanks! It’s good to be back.” Hailey said as she looked over to Jay. She was now noticing the woman that Jay was talking to.

“Hey partner!” She said, hoping to draw his attention.

“Hey. How was your date?” Jay asked. Will took notice of the daggers that Hailey was shooting at Jay with her eyes. For her part, Hailey was fed up with Jay’s attitude.

“What the hell are you talking about?” She shot back. Just then she felt a hand on her back. 

“Alright, what are we drinking?” OA asked. Will looked down at Hailey hoping for an introduction.

“Hey there! OA. I’m Hailey’s partner from New York.” Jay couldn’t stop the scoff that came out of him. Hailey and OA looked over at him but before they could react, Will stepped in.

“Will Halstead. Nice to meet you.”

“Halstead? Any relation?” OA asked motioning between Jay and Will.

“Brothers. Although most would say I’m the smarter one.” Will joked hoping to lighten the mood, but seriously, what the hell was Jay’s problem? Hailey watched as Jay turned away from them, returning his attention to the woman he was with.

“Whiskey. We are drinking whiskey tonight.” Hailey said, turning to OA to answer his earlier question.

“You gonna be good to drive?” OA asked concerned. In the time he had known Hailey, whiskey was her go to on particularly hard days. Jay also took note of Hailey’s response to whiskey and turned back to them. Hailey reached into her pocket and took out her keys, handing them to OA. 

“You’ve got an early morning, right? You can drive me home.” OA’s eyes widen at her statement. He knew that she meant he couldn’t drink too much tonight, but he still couldn’t help but feel like the two men with them might get the wrong idea.

At that moment, Jay had decided he had enough of the conversation. He stood up, grab his beer and leaned in to say something in Candie’s ear. He then walked off to a booth in the corner of the bar, Candie following behind him. Hailey watched as they sat opposite from each other and Jay began talking to her. 

“So, New York?” Will asks, trying to move the conversation along.

“Ya. Lived there my whole life.”

“I lived there for a few years. Worked in a plastic surgery clinic in Manhattan.”

“Ah, so you were living the good life!” OA joked. “Tell me, how did you feel about the pizza?” Hailey rolled her eyes as Will laughed. He wasn’t in on the inside joke, but he had spent enough time in New York and Chicago to know exactly what OA was asking.

“I prefer Chicago pizza myself, but there were a few hidden gems in New York that I enjoyed.” As their drinks arrived at the bar, Hailey invited Will to join them with the rest of Intelligence. Will looked over to Jay, who had moved closer to the wall and now had Candie sitting beside him.

“Ya. Thanks.” He said as he grabbed his beer and moved over to join the unit. 

Hailey tried her best not to look over at Jay and his new friend. She kept finding herself trying to turn to look but luckily was able to stop herself before she did. She tried to focus on the group. OA was telling them a story about how they chased a shooter through New York, which resulted in Hailey jumping on top of a car and running across the hood. Everyone on the team was laughing and enjoying their time. The group did not go unnoticed by Jay. He watched the way Vanessa and Kim stared at OA like they were heart eye emojis. He watched as Adam hung on his every word. He watched as Kevin’s jaw hung open as he listened to the stories OA was telling. He tried not to look at his team. Tried to focus on the lady that was sitting next to him. She was saying something, he wasn’t sure what. She was sitting closer now. He felt her hand on his leg which finally got his attention. 

Hailey meanwhile was trying her hardest to ignore the need building up in her to go to the bathroom. She knew that she would have to walk past Jay’s booth to get there, but she was not sure that she could handle seeing him. She managed to avoid it for an hour before she finally couldn’t wait any longer. She drank the rest of her whiskey and excused herself. She pulled out her phone, hoping that it could distract her from the booth. 

Jay watched as she fumbled with her phone when she passed the booth. He knew that Hailey could hold her liquor, but he also knew the tell-tale signs of when she was nearing her limit. Seeing her struggle with the hand-eye coordination was a red flag for Jay. As he watched her head towards the bathrooms, he excused himself from Candie, hoping to catch Hailey. 

In the bathroom, Hailey took a minute to splash some water on her face. This day had not gone as she planned, and she could not possibly be more disappointed. She was hoping to be the one on Jay’s arm tonight, but instead had to spend the night trying not to look at him and a random female pawing at each other. She looked at her reflection in the mirror and felt her senses starting to dull. Her eyes looked dazed, which would help explain the burly vision she was starting to feel. Sounds around her were too far away for her to focus on. She realized that she had reached that point in the night where she needed to cut herself off. As she walked out of the bathroom, that’s exactly what she intended to do.

She made it halfway down the hallway before she felt herself walk into someone. She looked up and realized that it was Jay, he had his arms on her waist trying to steady her. Is he was saying something? She tried to focus on his words but she couldn’t pull her thoughts out of how it felt to be in his arms.

“Hailey! Are you listening to me?” Hailey noticed the concern in Jay’s voice.

“Hmm? Ya, sorry. What?” Smooth, she thought to herself. Hailey took a step back and tried to steady herself. 

“I said are you ok? How many drinks have you had?” Jay couldn’t hide the irritation in his voice. Some partner, he thought. She should have been cut off a couple of drinks ago. 

“I’m good.” She tried to say confidently. She knew the answer was too many.

Before Jay could get another word out, he felt a pair of arms wrap around his waist. Suddenly he was spun around, and the hands moved quickly to wrap themselves around his neck. Jay watched in horror as Hailey stormed off after Candie asked him if he wanted to get out of there. Why was she mad? What did he do?

Hailey returned to the group in a huff. She jumped up on her stool and grabbed for one of the shots that had appeared at the table. She downed one, then another immediately after. OA looked at her with concern. He put an arm around her waist and leaned down to whisper into her ear. 

“Maybe we should slow down Chicago. We’ve got a fun day of work planned for tomorrow.” OA said trying not to make Hailey feel like he was telling her what to do. Jay, who had followed Hailey after turning Candie down, stopped in his tracks when he witnessed the exchange. He dropped his head in defeat and turned to walk to the bar and settle his tab. He stood with his back turned to the Intelligence table hoping that he could get out of there before he saw Hailey and OA leave together. 

After giving OA’s words some thought, Hailey decides that it is time to call it a night. Her somber mood and rapid alcohol intake had not gone unnoticed by Will. He couldn’t help but feel angry at his brother. He knew how Jay behaved when he was jealous, and he was positive that Jay had jumped to conclusions about Hailey and OA. He watched as Hailey attempted to step down from the high stool she was on. She missed her footing and ended up stumbling over her feet.

The whole table jumped to their feet as they watched her begin to fall. The noise roused Jay’s attention who turned just in time to see OA grabbing Hailey and catching her halfway through her fall. He pulled her up, arms around her waist attempting to steady her on her feet.

“Easy Chicago” OA said with concern laced in his words.

Will was at her side instantly, hands on her shoulder to aid in steadying her. 

“Hailey?” Will asked trying to get her attention.

“I’m good. Sorry, I got up too fast. Lost my footing. I’m fine.” She said, speech slightly slurred from the excess alcohol consumption. Will shot OA a concerned look as he began to grab their coats to leave. The next thing Hailey knew, she felt another set of hands on her back. She turned to see Jay standing beside her, looking at her concerned.

“Hails, you good?” Jay asked worried. 

“I’M FINE” Hailey harshly responded to Jay as she moved away from him. It was a move she would come to regret as the room started to spin from how rapid movements.

“Vanessa, can you take me home please?” She asked her roommate, desperate to escape the current scene unfolding in the bar.

“Of course.” Vanessa responded softly as she walked to her side. 

“Here.” OA said helping Hailey into her coat. “Let’s go.” He was ready to call it a night as well. That was the last straw for Jay.

“She asked Vanessa to take her not you.” Jay said loudly as he stepped closer to OA, pushing his hands away from Hailey. At that, OA took a step towards Jay and stood straight, puffing out his chest. His cold stare met Jay’s angry eyes as the rest of the group scrambled to get in between them. Vanessa had already started walking Hailey out of the bar by the time Kevin and Adam were trying to keep OA and Jay separated. After one swift push from Kevin telling OA to walk away, OA shook off his anger and turned to leave. As much as Kevin liked OA, Jay was his brother. If something was going to go down, there was no question which side he was on. 

When he got outside, OA found Vanessa trying to lean Hailey against a wall. He ran over to them to help.

“I gotta go get my car. She said she is going to throw up.” Vanessa said concerned.

“I’ll wait with her.” OA assured Vanessa as she ran off to get her car. OA held Hailey as her body racked with sobs. She cried for her disappointment at seeing Jay with someone else. She cried at her missed opportunity to tell him how she felt. She cried at her loss of control on her first day back in Chicago. She cried for drinking too much. She cried for the embarrassing scene she had caused. And she cried because it was the only thing she could think to do. 

“I feel like I’m in fucking high school. I can’t believe I’m getting drunk and crying over a boy.” Hailey cried out. 

Before OA could say anything, Hailey was pushing herself away from him and bending over to throw up. OA crouched down and held her hair back while rubbing circles on her back. Jay watched the scene unfold from Molly’s window. He could hear Will yelling something at him, but he did not know what it was. He could not focus on anything but Hailey falling apart in front of him. Knowing that he had caused it. Knowing that he was the one that pushed her into OA’s arms. 

Vanessa pulled the car around and OA helped Hailey walk to it. He opened the door for her and gave her a firm hug before helping her in. Vanessa turned to him and gave him a well-earned fist bump as she ran over to her side of the car. When OA turned to walk back to the bar, he saw Jay walking towards him. In that moment, he became consumed with anger. He watched as Kevin and Will exited the bar trying to get Jay’s attention, unsuccessful as Jay kept advancing towards him.

As the two men got closer to each other, Kevin and Will began to run, hoping to get to them before they reached each other.

**Notes for the Chapter:**

> I hope you enjoyed. We are looking at 2 more chapters after this! I am really hoping to cap it at that but the more I write, the more story I find to tell!


	4. Chapter 4

**Notes for the Chapter:**

> Thank you again for all the support! I enjoy reading you’re comments and I am glad that you are enjoying this. To be honest, I was very concerned that people would be upset at the way I wrote Jay versus the way I wrote OA. I tried to give insight into Jay’s thoughts so that people could see that he knew he was being a jerk and felt terribly about it, but couldn’t help himself since he was consumed with jealousy. Not saying that makes it ok, but he is only human (I mean, as much as a fictional tv character can be) and we all have our bad moments.

“WHAT THE HELL IS YOUR PROBLEM?!” OA yelled at Jay as he shoved the man in front of him. 

“YOU’RE MY PROBLEM!” Jay said as he returned OA’s push with one of his own. 

The two men balled up their fists and raised them, hoping to get at least one hit in before they got separated. Unfortunately for Jay, OA was able to connect first with a swift punch to the jaw. When he went in for another hit, Jay was able to duck down and charge into OA knocking him to the ground. 

Before Jay could get a hit in, however, Kevin and Will had reached the two men. They were able to pull Jay off of OA before OA was able to recover and get on his feet. While Kevin tried to keep OA away from Jay, Will was trying to keep his brother back. 

“JAY! Come on!” Will said as he tried to push Jay back towards Molly’s.

“Do you know what you did?” OA yelled at Jay as Kevin kept trying to push him away.

“What I did? You were the one with her! You’re the one that let her drink too much! I’m sure you’re disappointed that you aren’t the one taking her home.” Jay yelled as he tried to charge through Will to get to OA.

“The only reason she is wasted is because you’ve been an ass since she got home.”

“I haven’t even seen her today, she spent all day with you.” Jay yelled as Adam and Kim now joined the group to try to deescalate the situation. With that comment, OA pushed himself off of Kevin and straightened himself out. Kevin held a hand out in front of him and issued a look to OA letting him know that an attempt to go around him would not end well from OA. The FBI agent held his hands up in the surrender posture and nodded at Kevin. He heard him loud and clear.

“She was with me because you were avoiding her. She spent all week talking about coming home, spending the day with you. That’s all she wanted, and you shot her down at every attempt. You lied about having to work when you had the day off. You made her feel like you didn’t want to be around her.” OA yelled breathlessly at Jay. 

At that moment Jay felt all eyes turn to him. He was too embarrassed to look at them, knowing full well that each face would show disappointment in how he had treated Hailey. 

“She was just trying to figure out why you were mad at her. Then we show up here and she gets to watch you and some random chick paw at each other while you ignore her all night.” 

“You’ve been all over her since the second you guys off the plane! Every time I look at you two you have got your arm around her! I’m supposed to just sit there and watch it? Smile like a jack ass?”

“ARE YOU KIDDING ME?! THIS IS ALL BECAUSE YOU ARE JEALOUS?”

Suddenly, the rest of the intelligence unit started to feel like this is a private conversation that they should not be witness to. Kevin nods to OA as he turns to walk away and stops to give Jay a pat on the back as he passes him. He looks to Will, asking with his eyes if he’s got Jay. Will nods in understanding. 

“You good brother?” Adam asks, not wanting to make any assumptions.

“Ya. all good.” Jay answers defeated. Adam and Kim pat Jay on the back as they leave to finish their night inside.

Jay runs his hands through his hair trying to process what OA said. He knew that he was hurting Hailey, he could see it in her eyes every time he turned down an attempt to spend time together. He was trying to protect himself from the pain of rejection. He kept replaying the day in his head. How had he misread the day so badly?

He walked over to the curb and sat down. He dropped his head into his hands and tried to think of where he went wrong.

Will looked down at his brother and couldn’t help but feel bad. He was a good guy; he had a good heart. He knew the way he was acting was out of character. He sat down next to his brother and tried to comfort him.

“What did I do?” Jay asked.

“You jumped to conclusions. All of this- this whole day-this night, all of it could have been avoided with one conversation.” A frustrated OA answered. 

“Look. I get.” OA said as he walked to join the men on the curb. “I don’t think you two realize it, but you feel the same way about each other.” Jay looked over OA, shocked that he knew about how he felt.

“The hugs, all the physical contact. It’s just how I am. I am not gonna lie and say that I am not unbelievably attracted to Hailey,” Jay felt his body tense “but I have known from day one that I didn’t stand a chance. She’s in love with you.” Jay looked surprised at OA as he continued to talk.

“I’m from a big family. Not just parents and siblings. I grew up with my grandparents, aunties and uncles, cousins and friends that were so close they became family. I grew up being taught that you show the people that are important to you that how you feel. Hugs, pats on the back, all of it, it’s how my family is. Hailey saved my life more times than I could count while she was in New York. She earned a special place in my life.” OA tried to explain to Jay, hoping he would see that there were no romantic intentions behind his actions. 

Jay took in his words. What he described was the opposite of what him and Hailey had grown up in. They didn’t grow up with hugs and physical affection. It suddenly made sense to him how he could misread all of OA’s actions.

Jay felt the moisture that been pooling in his eyes begin to fall. 

“It was so hard to see her with another guy’s arms around her. Every time I see her, I just want to reach out and hold her.” Jay begins to say quietly. “I’ve always been so scared of how she would react. Sometimes she looks at me and I feel like she is begging me to reach out and hold her, but she always pulls away. When she came off the escalator, I saw her arms out like she wanted a hug, but I froze. I was scared of being rejected.” Jay shook his head in frustration.

OA, feeling sorry for this man he had only known for 12 hours, laid a hand on Jay’s back in an attempt to comfort him.

“I don’t know how to fix this.” Jay stated in a defeated voice.

“You tell her you’re sorry. You tell her how you feel.” OA said matter of fact.

“Luckily for you, she knows you’re an idiot.” Will deadpanned. “And she knows that gets more obvious the more you drink.” Jay laughs at Will’s accurate description.

“Don’t make her wait all night with this on her mind.” OA’s voice was laced with concern as he tried to encourage Jay to reach out to Hailey. 

“Come on. I’ll drive you to Hailey’s.” Will said as he stood up and extended a hand to his brother to help him up. Jay nodded in agreement as he stood up and turned to OA. He ran a hand through his head, not sure of what to say to the man that had helped him despite the fact that Jay had been an ass all day.

“Look, I’m sorry.” Jay said as he extended a hand to OA.

“Me too.” OA said as he gave Jay a firm handshake. “I’ll be around for the week. I hope we can see each other again under more friendly circumstances.” OA said as he said goodbye to Jay and Will. 

“You ready?” Will asked as he squeezed his brother’s shoulder. Jay nodded in response. “Alright. Let’s go get your girl.” 

The ride home from Molly’s seemed to take forever, for both Hailey and Vanessa. Hailey had her head in her hands, eyes squeezed shut in an attempt to keep the nausea at bay. Vanessa was trying to figure out what had happened to bring Hailey to this point. Obviously, it had to do with Jay. She knew how excited Hailey was to see him. And when she had asked her how it went with Jay earlier that day, she was surprised at the way Hailey deflected the question. Vanessa knew that could only mean one thing, that it did not go well.

Vanessa was trying to figure out what could have possibly happened to derail the big plans Jay and Hailey had for each other. She knew Jay was just as excited to see her. He had taken the day off and when he wouldn’t say what his plans were for the day with Hailey, Vanessa knew it meant he was wanting whatever it was to be just between him and Hailey. She hoped this meant telling her how he felt, and Vanessa was on board for this plan. As she pulled into her parking spot, she looked at her roommate who was folded over with her head in her lap and sniffling quietly. 

“We’re home Hailey. Are you good to walk?” 

“I think I can make it inside. Just, I can’t open my eyes. Can you just bring me to the bathroom?” Hailey managed to say.

“Hailey, what happened?”

“I don’t know.” Hailey said in a low whisper. “I don’t know. He was avoiding me. All day. He lied about having to work. He wouldn’t go to dinner with me and OA and then when I saw him at the bar, he asked me how my date with OA went. He was with some girl at the bar.” Hailey was trying to answer without breaking into tears again. Vanessa nodded along in understand. She was pretty sure she knew what was happening and she was not happy about it.

Vanessa let out a frustrated sigh then softly turned to Hailey. She placed her hand on her back, shaking her head at how her roommate could be so clueless. 

“He’s jealous Hailey.” Vanessa’s words were shocking enough to Hailey to make her turn to Vanessa and open her eyes.

“Of what?” Hailey asked confused.

“Hailey. Have you seen OA?” Vanessa chuckled as she asked her roommate the obvious question.

“The man can fill out a suit in all the right places. It couldn’t be easy for Jay to see that this is the person you were running around with day and night in New York.” 

“No. Jay wouldn’t, no. No. He knew all about OA. He never had a problem or seemed upset the entire time I was gone and would talk to him about OA.” Hailey was trying to rack her brain looking for the clues. A task that would be infinitely easier if the dame car would stop spinning. 

“That was before he knew what he looked like.” Vanessa thought very hard about how to choose her next words. “Hailey, I’m not saying anything Jay did today is ok, but you and OA seem to have a very flirtatious partnership. In the 2 hours we were together at Molly’s , I saw you and OA touch more than I have seen you and Jay touch all year.” Vanessa paused to gauge Hailey’s reaction. The last thing she wanted to do was make Hailey feel bad or like any of it was her fault. “I think Jay got the wrong idea.”

As the realization of what had happened that day became clear to Hailey, she felt her stomach jump.

“I’m gonna be sick.” She said as she opened the car door and jumped out to throw up. Vanessa shook her head at the sight of her best friend. She got out of the car and helped Hailey into the house. She walked her to the bathroom and helped her lay against the bathtub next to the toilet. She went to the hall closet and got some sheets together to make up the couch. She knew there was no way Hailey was making up the stairs and this would be more comfortable for her. She returned to the bathroom to sit on the floor with Hailey as she waited for the nausea to subside so she could walk. 

After about 15 minutes of leaning against the bathtub, both women began to drift off to sleep. As Vanessa felt her head start to bob, she was startled awake by the loud knocking at her door.

**Notes for the Chapter:**

> I think I can wrap up this story with one more chapter, but who knows?! There still feels like a lot of story left to tell and I’m already halfway through chapter 5. Jay hasn’t even made it past Vanessa yet, so their may be a really long chapter or 2 smaller ones. Thank you for reading!


	5. Chapter 5

**Notes for the Chapter:**

> Thank you again for reading and commenting! I enjoy reading the reactions to the story! I thought the conclusion would be a lot longer, but as I was writing, I realized that so much of their story has already been told, we deserve to get to the good stuff! I hope you enjoy! As always, thanks to the Let’s Talk Upstead group chat on Tumblr for the support! 

As she stood up and made her way to the door, all the sympathy and compassion Vanessa had for Jay started to disappear. The closer she got to the door, she was positive it was Jay on the other side, the more anger built up in her. Anger for her friend who was hopelessly in love, anger for the pain she was being put through, anger for how a simple misunderstanding had spiraled into the mess that was their night at Molly’s, and anger at Jay for not being able to admit his feelings. In that moment, as she reached for the door handle, all common sense and logic left her body. No longer did she see two people that were too afraid to admit their feelings for each other who got tangled in a confusing web of misunderstandings. No, as she opened the door and saw Jay standing there, a bruise forming around a cut on his lip, what she saw was the man responsible for making her best friend cry. 

When she opened the door, she thought she was gonna unleash a tidal wave of fury on Jay. She stepped outside, an act which made Jay take a couple of steps back as Vanessa shut the door behind her. She stood there, arms folded across her chest and stared Jay down. Jay couldn’t help but feel like a kid getting ready to be scolded by his mom. He looked at her wide eyed, not knowing what to expect but knowing whatever it was, he deserved.

“Is she ok?” Jay finally managed to say.

Vanessa did not answer. She simply maintained her stance trying to compose herself. She knew Jay wasn’t completely at fault for what had happened; the last thing she wanted to do was explode on him. She racked her brain for what to say and how to say it. She didn’t trust herself to open her mouth and have anything other than screams come out. 

“I just want to talk to her.” Jay said looking to the ground. 

Vanessa took a deep breath in and looked Jay up and down. She noted his slumped shoulders. His hands in his pockets. The way he could not seem to hold his head up. The way he struggled to look her in the eye. In that moment she knew that there was nothing she could say or do that would make him feel any worse than he already did. She breathed in deeply again as she felt the anger leave her body and be replaced with sympathy for another one of her friends that was hopelessly in love. 

“OA I assume.” Vanessa asked softly as she pointed to Jay’s jaw.

“Uh. Ya.” Jay said, embarrassed as he recalled the night’s events. “Can’t blame him though.”

Vanessa nodded at Jay’s statement. She let out another deep breath and then reached her hand out to Jay’s shoulder. She instantly felt the tension in Jay’s body leave. She chuckled at the thought of the war vet, one of the strongest and bravest people she knew, fearing her. 

“She’s not ok.” Vanessa said as she turned and opened the front door. She stepped aside and waved an arm for Jay to enter. Jay nodded at her as he walked in.

“She’s in the bathroom. She’s been throwing up. I made up the couch for her, she said she couldn’t make it to her room.” Vanessa said as she walked towards the bathroom. She held out a finger indicating to Jay to wait for a moment. She went into the bathroom and crouched down next to Hailey who was resting her head on the edge of the bathtub.

“Hailey. Jay is here. Do you want to talk to him?”

“Not really.” Hailey mumbled. The last thing she wanted was for Jay to be witness to her current state.

“Do you want me to tell him to leave?”

“No. Don’t.” She attempted to lift her head to straighten herself out. “Can you get me some mouth wash really quick before you let him in?” Hailey figured the least she could do was to not smell bad for this conversation. Vanessa chuckled and helped her rinse her mouth out. She gave Hailey a quick hug before she left. 

“Good luck.” Vanessa said as she walked around Jay to go to her room. She had no idea what was going to happen, but as she walked up the stairs, she said a little prayer for Jay to still be there in the morning when she woke up. 

Jay found himself frozen in place. He wasn’t sure that he could handle seeing the aftermath of what happened at Molly’s. He approached the bathroom tentatively and as he slowly pushed the door open; he felt his heart drop when he saw her.

“Hey.” Jay said sheepishly. He watched as Hailey tried to lift her head off the edge of the bathtub. Before she could shift her body to sit up straight, Jay was rushing to her side, scared she would fall over. 

“Don’t sit up Hails.” He said to her as he crouched down next to her and reached out to move her hair behind her ears. 

“Mmhm” Hailey hummed as she leaned into his touch. “I think I over did it.” She chuckled weakly.

“Ya. You definitely did.” Jay said as he sat on the floor next to her. He looked down at her hand which was resting on her lap. Just as he was about to reach for it, Hailey began to speak again.

“There’s nothing going on with OA.”

“Hailey, you don-“

“No. Jay. I need you to know. I’m not interested in anyone else.” Jay nodded at her to let her know he heard her. He reached down and grabbed her hand.

“I’m really sorry, Hails. I was a jerk today.” He whispered quietly.

“Ya, you were.” Hailey said with a chuckle. She might be drunk, but she wasn’t passing up an opportunity to call Jay out for his behavior. “I don’t do jealous, Jay. You need to know something, just ask.” She said as firmly as she could in her state. 

Jay nodded in understanding. 

“I wish I could redo this day. Do it right.” Jay said shaking his head. “I was just so jealous.” Jay thought hard about his next words. “I’m not that guy.” He said shaking his head. “Going forward, I can promise you that I will never make you question how much I trust you.”

That was when Hailey noticed that Jay had grabbed a hold of her hand. She shifted hers so that fingers could be intertwined. They sat there for a minute staring at their hands. They had so much to say but for some reason, just sitting there on the bathroom floor and holding hands seemed to be enough. 

“I really hope you aren’t planning on kissing me tonight.” Hailey deadpanned, but in all seriousness, she was very worried he would. Jay laughed at her boldness.

“You know,” Jay said as he looked her in the eyes “I was.” Hailey groaned and tried to playfully swat at him.

“Jay. I’ve already thrown up twice. This is not how I want this to happen.” Hailey said trying to reason with him.

“So, you’ve thought about how this would happen?” Jay said cheekily, raising an eyebrow at Hailey’s revelation.

“Yes.” She answered with a matter of fact tone. “and none of the scenarios took place on a bathroom floor.” She said as she looked pleadingly at Jay. He reached out and placed a hand under her chin, rubbing his thumb against her cheek. It was taking everything he had not to lean over and kiss her, but he wanted to respect her wishes.

“Ok.” He said softly. “You think you’re ready to move?” Jay asked. Hailey broke eye contact and looked out the bathroom door. The couch seemed so far away, and she wasn’t sure that she was done throwing up.

“I can carry you.” Jay said, noticing her hesitation. 

“Ok. I’m ready.” She said. Jay stood up and slowly pulled Hailey to her feet. With one arm supporting her back, Jay bent over and used his other arm to scoop Hailey up. He began walking to the couch when Hailey stopped him.

“My room please.” She said as she closed her eyes and buried her head into Jay’s shoulder. He turned and began going up the stairs, passing Vanessa’s room on the way to Hailey’s. Luckily for Hailey, he was familiar with the lay out after helping the two women move in, which meant she didn’t have to keep her eyes open to give directions. When he reached her room, he set her on the bed and took her shoes off. Hailey took a pillow and held it over her head, hoping the act would make everything stop moving. Jay had sat on the bed while trying to adjust her sheets for her so she could be comfortable. When she felt the weight shift on the bed, she realized he was leaving.

“Are you leaving?” 

“I was just going downstairs. I was going to take the couch, if that’s ok.” It would not have been the first time Jay slept on the couch, so he didn’t think it would be a problem.

“Stay in here.” Hailey responded. “Please.”

“Hailey, you’re drunk.” Jay said worried that she wasn’t fully aware of what she was saying.

“Just sleep here Jay. I might need help getting up; you can help hold my hair back.” She joked, hoping to make Jay feel more comfortable. With the pillow still over her head, she couldn’t see Jay’s reaction. As the silence grew longer, she began to worry that she had made him uncomfortable. Just as she was about to move the pillow away, she felt the bed dip on her right side as Jay laid down. 

Hailey smiled as her hand began to fumble around the mattress looking for Jay’s. When he noticed, he moved closer so that he could reach an arm behind her back, moving her closer to him. He listened as Hailey’s breathing began to get deeper and deeper, knowing she was falling asleep.

“Let me know if you need to get up.” He whispered as he lifted the pillow slightly so she could hear him.

*************

A few years later during her maid of honor speech, Vanessa would tell the crowd of how it took a right hook to the jaw to knock some sense into Jay. As they laughed, Jay would lift his glass towards OA who would return the gesture, understanding what was being said. She joked about how she had no idea when she let Jay into the house that night that he would never leave. How Jay and Hailey hadn’t been apart since then. She expressed her genuine gratitude towards Jay for loving Hailey as much as she deserved to be loved. She cried as she told Hailey she was the big sister she always dreamed of having. She laughed as she the crowd cheered when Hailey and Jay shared a kiss. 

And she said another little prayer, thanking whoever it was that heard her prayer that night as she was walking up the stairs for answering it.

**Notes for the Chapter:**

> I hope you enjoyed! I kept going back and forth while writing this fic about how I wanted it to start. I wanted to write something with Jay and OA meeting and came up with 2 different ideas. I decided to make the other idea into a fic also, so I am hoping to get that finished up so I can start posting sometime next week. I hope you guys aren’t burnt out on OA coming to Chicago yet. 😉

**Author's Note:**

> Thank you for reading! I hope you enjoyed! There will be one, maybe two more chapters! I struggled with Hailey and Jay being OOC. Although I feel like Hailey would call Jay out on his jealously, the girl is also head over heels so I think she may have a bit more patience!


End file.
